Citric Acid → 3-(1H-indol-3-yl)-2-(1-methyl-1H-indol-3-yl)-N-methylmaleimide

HRID 1357095Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1357095
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([Mg]Br)C.Br[C:15]1[C:16]([N:18]([CH3:32])[C:19](=[O:31])[C:20]=1[C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]([CH3:30])[CH:22]=1)=[O:17].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1(C)C=CC=CC=1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:15]2[C:16](=[O:17])[N:18]([CH3:32])[C:19](=[O:31])[C:20]=2[C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]([CH3:30])[CH:22]=2)=[CH:2]1

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 798IndoleHCID 98184713-Bromo-1-methyl-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dioneHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 99285773-(1H-indol-3-yl)-2-(1-methyl-1H-indol-3-yl)-N-methylmaleimideAusbeute 96,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of indole (66 mg, 0.21 mmol) dissolved in toluene (1 mL) was added 0.95M ethylmagnesium bromide (0.5 mL, 0.47 mmol) at 40 ° C., and the whole was stirred at 40° C. for 45 minutes. Successively, a solution of 2-bromo-3-(1-methyl-1H-indol-3-yl)-N-methylmaleimide (66 mg, 0.21 mmol) dissolved in toluene (3 mL) was added thereto, followed by stirring under heating and refluxing for 2 hours. After 20% aqueous citric acid solution (1 mL) was added thereto under ice cooling and the whole was stirred, toluene was removed by concentration under reduced pressure and the resulting concentrate was extracted with ethyl acetate. The extract was dried over sodium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography over silica gel (ethyl acetate:n-hexane=1:1) to obtain 3-(1H-indol-3-yl)-2-(1-methyl-1H-indol-3-yl)-N-methylmaleimide (71 mg, 96.8%) as red solids.

Aufarbeitung

  1. additionwas added
  2. stirringby stirring
  3. temperatureunder heating
  4. temperaturerefluxing for 2 hours
  5. stirringunder ice cooling and the whole was stirred
  6. customtoluene was removed by concentration under reduced pressure
  7. concentrationthe resulting concentrate
  8. extractionwas extracted with ethyl acetate
  9. dry with materialThe extract was dried over sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by column chromatography over silica gel (ethyl acetate:n-hexane=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-ad7973cc35ac4ca39994061609ebab57
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06589977B1

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